Why this Deadline will be different for Montgomery

July 3rd, 2023

This story was excerpted from John Denton’s Cardinals Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

Drafted, developed and nurtured by the Yankees throughout his first eight years in professional baseball,  was admittedly stunned to his core when he was dealt to the Cardinals before the MLB Trade Deadline last August.

Further complicating matters was the fact that Montgomery’s now-wife, McKenzie, had just started her residency as a dermatologist in New York and would also have to pick up and move halfway across the country to where Jordan’s baseball career was headed.

Realizing the shock that Montgomery was in after getting traded from the only organization he had ever known, then-Yankees teammates Matt Carpenter and DJ LeMahieu tried to calm the left-hander's fears by giving him a scouting report on St. Louis and the Cardinals.

“Carp told me there was a really good culture here and that all the guys were great,” recalled Montgomery, who held the Yankees to just two hits and one unearned run over 6 2/3 innings of a 5-1 Redbirds victory at Busch Stadium on Sunday. “DJ told me about Nolan [Arenado] and how great of a teammate he is. Baseball has such a weird web, and everybody is connected. So, there’s always somebody looking out for you when you’re the new guy.”

No longer the new guy after 11 months in town, Montgomery has made a nice home for himself in St. Louis. After shutting down the Yankees for a second time in as many seasons and reminding them of the folly in making a 6-foot-6 pitcher available at the Trade Deadline, Montgomery won a fourth straight decision and his ERA plunged to 3.28 -- the ninth-lowest mark in the NL.

Montgomery’s record is a pedestrian 6-7, but that’s more a product of poor run support than it is him being ineffective.

Montgomery has been the steadiest pitcher on a Cardinals team that has struggled to find much consistency. With the Redbirds sitting 9 1/2 games out of first in the NL Central, they have four weeks to decide whether they will be buyers or sellers at this year’s Deadline.

Team president John Mozeliak gave a glimpse into his thinking last week, saying: “I would hope that the Cardinals are not allowed to rebuild. We have an amazing fan base, and we know we’re not where we want to be, and we have to make some changes, and we’re going to try. … As for a message to the fan base, we’re not looking to blow up this team; but we are looking for ways to improve this team.”

The Cardinals dramatically improved their team at the Deadline last August by dealing for Montgomery and fellow pitchers José Quintana and Chris Stratton. That helped them eventually overtake the Brewers and win the NL Central in runaway fashion.

This time around, Montgomery and fellow starter  are two of the Cardinals' most prominent free agents-to-be in the offseason. Do the Cards supplement the staff around Montgomery and Flaherty and hope for some late-season magic? Or, believing this season is already a lost cause, do they move them before the Deadline and get pieces for a potentially better 2024?

Montgomery and his agent, Scott Boras, let the Cardinals know last winter they were open to discussing a contract extension with the club, but those talks never materialized. The pitcher is very hesitant to talk about his long-term future, saying only this: “I told them that’s not my decision [as far as returning to the Cardinals]. I said it in spring [that he wanted to stick with the Cardinals]. We’ll see what happens in free agency.”

Whatever happens -- in free agency or at the Aug. 1 Trade Deadline -- won’t catch Montgomery as off-guard as he was last August when he was dealt from the Yankees to the Cards. He had to adapt quickly after getting traded, and he believes he’s a better pitcher now after getting knocked out of his comfort zone in New York and shipped to St. Louis.

“I’m not in control of my life and I believe firmly that [the trade] happened for a reason,” he said. “You can either be sad about it or try and make an imprint here, especially with young guys like [Matthew Liberatore] or anyone in general. I just want to try and make an imprint on someone else’s life.”